Br[C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]#[N:5].[CH3:14][C:15]([CH3:20])=[CH:16]B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:10][C:9]1[C:2]([CH:14]=[C:15]([CH3:20])[CH3:16])=[C:3]([C:6]([N+:11]([O-:13])=[O:12])=[CH:7][CH:8]=1)[C:4]#[N:5]
2-Bromo-3-fluoro-6-nitrobenzonitrile (Example 134d) (0.62 g, 2.53 mmol), 2-methylprop-1-enylboronic acid (0.50 g, 5.05 mmol), palladium(II) acetate (0.023 g, 0.102 mmol), K3PO4 (1.61 g, 7.58 mmol), and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.083 g, 0.202 mmol) were suspended in anhydrous THF (16 mL) under nitrogen and heated at 70° C. for 4.5 h. Solvent was removed under vacuum, and the product was purified by chromatography on silica gel eluting with gradient 0% to 100% ethyl acetate in hexanes, to give 3-fluoro-2-(2-methylprop-1-enyl)-6-nitrobenzonitrile 0.44 g (78%) as a yellow solid. MS 221 (MH+).
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